For the past few years, Hugh Bob And The Hustle have been a reassuring and reliable Milwaukee music presence, effortlessly playing no-nonsense, honkey-tonk-indebted country to any bar full of buzzed patrons willing to listen. The group’s memorable 2012 self-titled debut (#49 on our list of the 50 best Milwaukee albums of the 2010s) doubled as a sort of origin story for frontman Hugh Masterson, chronicling his roots in one of Wisconsin’s most far-flung northern regions (“Ashland County”), a life-changing move to Milwaukee (“Milwaukee Man”), and endless nights spent nursing a drink or three (“This Bar Is A Prison”).

Masterson’s story will soon include another chapter, as the singer-songwriter prepares a move to Nashville, Tennessee to pursue further opportunities in the country music. Before a going-away show December 12 at Cactus Club, Milwaukee Record reached out to Masterson via email to talk about writing on Nashville’s Music Row, quality cottage cheese, and the future of his band.

Milwaukee Record: Maybe this is a question with an obvious answer, but why Nashville? When did you make the decision?

Hugh Masterson: I have lots of musician friends in Nashville, and they’ve all been trying to get me to move for a couple of years. I’ve been getting down there often and I feel very inspired by how many talented people are in one city, or at times just in one room. Everyone is really supportive and encouraging and I always meet new people and make more connections. I drove to Nashville after SXSW and had a week there doing interviews and co-writes. I’d go from meeting and following Roseanne Cash on WSM to co-writing on Music Row and then over to meet up with the VP of CMT. Then I’d go out and drink bourbon with my friends at a bar packed full of musicians 20 times better than me, sometimes making it to an after-party to play more music. I’m sure that week was when I realized I needed to be there.

MR: You’re one of a handful of Milwaukee musicians who have recently left, or are planning to leave. (Todd Umhoefer of Old Earth, Jordan Maye of the Breadking collective.) Are there just not enough opportunities in Milwaukee for career-minded musicians?

HM: I’m not sure why those folks left or what their plans are. We could all end up back here the same as we sometimes leave. I love Milwaukee, that’s why I’ve been here for 15 years. I just need a change for whatever reason and the place I need to go is Nashville. I’m sure there are opportunities here that I’m not even aware of. For me, I know there is a lot more opportunity down there to write, record, network with people doing similar things as me, etc.

MR: You’ve said in another interview that the Hustle will continue. How will that work? How did the band react when you told them the news?

HM: Yes, my band is very important to me and they’re all amazing musicians and people. We just won’t do one-off dates unless they make sense, and I’ll come back and practice before tours. I can also send them demos for new ideas and we can work through that when I’m back as well.

I told the guys that I was thinking it might be a good idea to try living in Nashville for a while, and they were all very supportive. If it seemed like it would complicate things too much, well, then I probably would’ve just squashed the idea. I’m just trying to keep this thing moving the best I can and get more opportunities for all of us.

MR: What are you going to miss most about Milwaukee and Wisconsin?

HM: I’ll miss being able to see my twin brother and his family, watching Packers games with my friends, Riverwest Stein, and quality cottage cheese.

MR: What can we expect from your goodbye show at Cactus?

HM: We’re planning on a fun, upbeat show! Our buddy Frankie Lee is going to open up for us. I’m sure I’ll be hugging everyone that crosses my path. It will be a celebration, no doubt. This city has been here for me and had my back for a long time. I’ll still consider Milwaukee home and I’ll be back fairly often, so let’s not act like I’m going to live on the moon. Nashville is only nine hours away. Come visit, and bring Stein and Pick ’n Save cottage cheese (low fat).

About The Author

Matt Wild
Co-Founder and Editor

In his spare time, Matt Wild enjoys collecting 8-bit Nintendo games (emulation is for creeps) and fondly remembering the time Milwaukee weatherman Vince Condella caused a stir at his Catholic grade school by showing up with an earring. He lives on Milwaukee's East Side.